CORTISONE

US Previously Marketed

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H28O5
Molecular Weight	360.444
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC(=O)[C@@]3([H])[C@@]2([H])CCC4=CC(=O)CC[C@]34C

InChI

InChIKey=MFYSYFVPBJMHGN-ZPOLXVRWSA-N

InChI=1S/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-15,18,22,26H,3-8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C21H28O5
Molecular Weight	360.444
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/009866s98_105lbl.pdf
Curator's Comment: description was created based on several sources, including: http://www.wikidoc.org/index.php/Cortisone | https://www.drugs.com/pro/cortisone-acetate.html | https://www.ncbi.nlm.nih.gov/pubmed/2811372 | https://www.ncbi.nlm.nih.gov/pubmed/7358829 | https://books.google.com/books?id=Q1voCAAAQBAJ&pg=PA113&lpg=PA113&dq=CORTISONE+SULFATE&source=bl&ots=-bwZTb4Fzh&sig=4gjBk9MhoF8OrL-7I5c06Fr32A8&hl=en&sa=X&ved=0ahUKEwiblMuT9pfVAhXK4SYKHXKKB6wQ6AEITTAG#v=onepage&q=CORTISONE%20SULFATE&f=false | http://www.google.com.pg/patents/US20120135924 | http://www.google.com.pg/patents/US20120128785 | https://www.google.com/patents/US4450151

Cortisone is a hormone that is FDA approved for the treatment of primary and secondary adrenocortical deficiency, rheumatic disorders, psoriasis, exfoliative dermatitis, bronchial asthma, allergic conjunctivitis, hemolytic anemia, enteritis, tuberculosis, trichnosis. Cortisone acetate binds to the cytosolic glucocorticoid receptor. After binding the receptor, the newly formed receptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing the increase in expression of specific target genes. Common adverse reactions include convulsions, increased intracranial pressure with papilledema, vertigo, headache, psychic disturbances, hirsuitism, glaucoma, exophthalmos. Aminoglutethimide may lead to a loss of corticosteroid-induced adrenal suppression. Co-administration of corticosteroids and warfarin usually results in inhibition of response to warfarin, although there have been some conflicting reports. Cortisone is a natural steroid hormone. Its sulfate analog has been detected in in umbilical vein blood fetus plasma between 19 and 32 weeks of gestation with a significant increase at 29-30 weeks and in amniotic fluid. Base on the experiments with rats it was suggested that cortisone sulfate in mammals could be hydrolyzed enzymatically liberating sulfate ions from cortisone. Cortisone sulfate has been proposed for use as one of the glycosaminoglycan compound materials in a cartilage prosthesis and biological nasal bridge implant manufacture as well as auxiliary agent in powder aerosol composition for use in baby powder, dry shampoo, water-eczema remedy and antiperspirant.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glucocorticoid receptor 172 Target ID: CHEMBL2034 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15705660	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Severe or incapacitating allergic conditions 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/009866s98_105lbl.pdf	Primary	Approved 8429	SOLU-CORTEF Approved Use Treatment of the Allergic states, Dermatologic diseases, Endocrine disorders, Gastrointestinal diseases, Hematologic disorders, Neoplastic diseases, Rheumatic disorders, Respiratory diseases, Renal diseases, Ophthalmic diseases, Nervous System Launch Date 1955
Rheumatic diseases 30 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/009866s98_105lbl.pdf	Primary	Approved 8429	SOLU-CORTEF Approved Use Treatment of the Allergic states, Dermatologic diseases, Endocrine disorders, Gastrointestinal diseases, Hematologic disorders, Neoplastic diseases, Rheumatic disorders, Respiratory diseases, Renal diseases, Ophthalmic diseases, Nervous System. Launch Date 1955
Primary adrenocortical insufficiency 7 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/009866s98_105lbl.pdf	Primary	Approved 8429	SOLU-CORTEF Approved Use When oral therapy is not feasible, and the strength, dosage form, and route of administration of the drug reasonably lend the preparation to the treatment of the condition, the intravenous or intramusculat use of SOLU-CORTEF Sterile Powder is indicated as follows: Primary or secondary adrenocortical insufficiency (hydrocortisone or cortisone is the drug of choice). Launch Date 1955

C_max

Value	Dose	Co-administered	Analyte	Population
477 nM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8284505	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		CORTISONE plasma	Canis lupus population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
1211 nM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8284505	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		CORTISONE plasma	Canis lupus population: HEALTHY age: ADULT sex: MALE food status: FASTED
4109 nM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6691888	44.8 mg 1 times / day steady-state, oral dose: 44.8 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		CORTISONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
23 min EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8284505	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		CORTISONE plasma	Canis lupus population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
16.2% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7195404/			CORTISONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:16962	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16962
ChemicalBook	CB6413305	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6413305
MolPort	MolPort-002-529-087	https://www.molport.com/shop/molecule-link/MolPort-002-529-087
ZINC	ZINC000004083557	http://zinc15.docking.org/substances/ZINC000004083557
eMolecules	29503844	https://www.emolecules.com/cgi-bin/more?vid=29503844
eMolecules	493549	https://www.emolecules.com/cgi-bin/more?vid=493549

PubMed

Title	Date	PubMed
Activities of 11beta-hydroxysteroid dehydrogenase 2 in different regions of the intestinal tract of pigs.	2001	11573149
Chemotherapy-related hemolytic-uremic syndrome following treatment of a carcinoma of the nasopharynx.	2001	11528253
Diagnosis of adrenal cortical dysfunction by liquid chromatography-tandem mass spectrometry.	2001 Apr	11337910
Adrenocortical response and cortisone replacement in systemic inflammatory response syndrome.	2001 Apr	11314835
Cervical intramedullar schistosomiasis as a rare cause of acute tetraparesis.	2001 Apr	11311476
Apparent mineralocorticoid excess.	2001 Apr	11306334
Intravitreal injection of crystalline cortisone as adjunctive treatment of proliferative diabetic retinopathy.	2001 Apr	11292410
The effect of structural QSAR parameters on skin penetration.	2001 Apr 17	11292537
Peroxisome proliferator-activated receptor-gamma ligands inhibit adipocyte 11beta -hydroxysteroid dehydrogenase type 1 expression and activity.	2001 Apr 20	11278270
Regression of neovascular iris vessels by intravitreal injection of crystalline cortisone.	2001 Aug	11558812
Efficacy of nonoperative treatment for lateral epicondylitis.	2001 Aug	11520020
Expression and putative role of 11 beta-hydroxysteroid dehydrogenase isozymes within the human eye.	2001 Aug	11481269
Ontogeny of 11beta-hydroxysteroid dehydrogenase: activity in the placenta, kidney, colon of fetal rats and rabbits.	2001 Feb	11294497
Use of salivary biomarkers in biobehavioral research: cotton-based sample collection methods can interfere with salivary immunoassay results.	2001 Feb	11087962
Lack of mutations of type 1 11beta-hydroxysteroid dehydrogenase gene in patients with abdominal obesity.	2001 Feb-May	11428721
[Present status of studies on pulmonary aspergillosis--special reference to the pathogenesis and progression].	2001 Jan	11400689
Congenital deficiency of 11beta-hydroxysteroid dehydrogenase (apparent mineralocorticoid excess syndrome): diagnostic value of urinary free cortisol and cortisone.	2001 Jan	11227727
11beta-hydroxysteroid dehydrogenase activity in human aortic smooth muscle cells.	2001 Jan	11213028
Human cervical tissue metabolizes the tobacco-specific nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, via alpha-hydroxylation and carbonyl reduction pathways.	2001 Jan	11159748
[Usefulness and necessity of unsynchronized photosolotherapy and bath-PUVA--two variants of balneophototherapy--in funded ambulatory health care].	2001 Jul	11512224
Lipoid congenital adrenal hyperplasia (CAH): patient report and a mini-review.	2001 Jul	11491137
Outpatient laparoscopic adrenalectomy in patients with Conn's syndrome.	2001 Jun	11591947
Activation of the hypothalamic-pituitary-adrenal axis in obesity: cause or consequence?	2001 Jun	11527096
Shock wave therapy for chronic proximal plantar fasciitis.	2001 Jun	11400894
Functional expression, characterization, and purification of the catalytic domain of human 11-beta -hydroxysteroid dehydrogenase type 1.	2001 Jun 15	11294832
Cortisol metabolism and the role of 11beta-hydroxysteroid dehydrogenase.	2001 Mar	11469811
Disorders of mineralocorticoid synthesis.	2001 Mar	11469810
[Polycystic ovary syndrome of extra-ovarian origin. Review].	2001 Mar	11294032
A mutation in the cofactor-binding domain of 11beta-hydroxysteroid dehydrogenase type 2 associated with mineralocorticoid hypertension.	2001 Mar	11238516
[Reducing the need for cortisone. Does eucalyptus oil work in asthma? (interview by Brigitte Moreano].	2001 Mar 29	11332011
Induction of 11beta-hydroxysteroid dehydrogenase type 1 but not -2 in human aortic smooth muscle cells by inflammatory stimuli.	2001 May	11377976
Regulation of expression of 11beta-hydroxysteroid dehydrogenase type 1 in adipose tissue: tissue-specific induction by cytokines.	2001 May	11316764
Sarcoidosis: old and new treatments.	2001 May	11312398
The 11beta hydroxysteroid dehydrogenase 2 exists as an inactive dimer.	2001 Nov	11576624
Intraocular injection of crystalline cortisone as adjunctive treatment of diabetic macular edema.	2001 Sep	11530068
Impaired antifungal effector activity but not inflammatory cell recruitment in interleukin-6-deficient mice with invasive pulmonary aspergillosis.	2001 Sep 1	11494166
Determination of natural corticosteroids in urine samples from sportsmen.	2001 Sep 15	11585134

Patents

Sample Use Guides

In Vivo Use Guide

Therapy is initiated by administering hydrocortisone sterile powder intravenously over a period of 30 seconds (e.g., 100 mg) to 10 minutes (e.g., 500 mg or more). In general, high dose corticosteroid therapy should be continued only until the patient’s condition has stabilized, usually not beyond 48 to 72 hours.

Route of Administration: Other

In Vitro Use Guide

With the highest concentration of cortisone that can be used under these conditions (owing to the limitation of solubility), namely 10 ug/ml., it is only possible to kill about 50 % of the lymphocytes in 46 hr; and, by extrapolation of the curve, that a concentration of about 10 mg/ml. would be required to kill 99 % of them.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:43:00 GMT 2023` Edited by `admin` on `Sat Dec 16 17:43:00 GMT 2023`
Record UNII	V27W9254FZ
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CORTISONE

Official Name

English

CORTISONE [USP-RS]

Common Name

English

17,21-DIHYDROXYPREGN-4-ENE-3,11,20-TRIONE

Systematic Name

English

Cortisone [WHO-DD]

Common Name

English

PREGN-4-ENE-3,11,20-TRIONE, 17,21-DIHYDROXY-

Systematic Name

English

cortisone [INN]

Common Name

English

PREDNISONE IMPURITY A [EP IMPURITY]

Common Name

English

NSC-9703

Code

English

HYDROCORTISONE IMPURITY B [EP IMPURITY]

Common Name

English

CORTISONE [MI]

Common Name

English

CORTISONE [VANDF]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175576